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MedKoo Cat#: 591808 | Name: Phenyl sulfide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenyl sulfide is a component of a compound that can have inhibitory effects on microbial growth.

Chemical Structure

Phenyl sulfide
Phenyl sulfide
CAS#139-66-2

Theoretical Analysis

MedKoo Cat#: 591808

Name: Phenyl sulfide

CAS#: 139-66-2

Chemical Formula: C12H10S

Exact Mass: 186.0503

Molecular Weight: 186.27

Elemental Analysis: C, 77.38; H, 5.41; S, 17.21

Price and Availability

Size Price Availability Quantity
25g USD 230.00
100g USD 310.00
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Related CAS #
No Data
Synonym
Phenyl sulfide; NSC 4568 NSC-4568; NSC4568
IUPAC/Chemical Name
Benzene, 1,1'-thiobis-
InChi Key
LTYMSROWYAPPGB-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
SMILES Code
C1(SC2=CC=CC=C2)=CC=CC=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenyl sulfide is a component of a compound that can have inhibitory effects on microbial growth.
In vitro activity:
In this study, three series of benzyl phenyl sulfide derivatives were designed and synthesized, and their antibacterial activity against eleven MRSA strains were evaluated. The results showed that two series of the synthetic compounds (5a-5l and 12p-12u) exhibit potent antibacterial activity against S. aureus and MRSA, with minimum inhibitory concentrations of 2-64 μg/mL. The structure-activity relationships are discussed and the mechanism of the antibacterial activity was shown to involve the destruction of the bacterial cell membrane. Finally, the MTT assay results suggest that the toxicity of compounds 5f and 5h is selective between bacteria and mammalian cells. Reference: J Antibiot (Tokyo). 2020 Feb;73(2):82-90. https://pubmed.ncbi.nlm.nih.gov/31723217/
In vivo activity:
The present study was planned to investigate the prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07), against topically applied SM induced pulmonary toxicity in mouse. Pretreatment with DRDE-07 (0.2 LD50) attenuated SM-induced changes at all time point tested. BAL fluid biochemical endpoints indicated epithelial and endothelial cell damages as evidenced by increase in BAL protein, LDH level and increased number of activated macrophages. The increased myeloperoxidase activity and β-glucuronidase level exhibited the degranulation of neutrophils due to SM toxicity in lung. Reference: Drug Chem Toxicol. 2016;39(2):182-9. https://pubmed.ncbi.nlm.nih.gov/26247826/

Preparing Stock Solutions

The following data is based on the product molecular weight 186.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lu K, Chen Q, Xu XF, Meng Y, Lin J, Chen WM. Novel benzyl phenyl sulfide derivatives as antibacterial agents against methicillin-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2020 Feb;73(2):82-90. doi: 10.1038/s41429-019-0257-x. Epub 2019 Nov 14. PMID: 31723217. 2. Hatano A, Okada M, Shimazaki K, Uehara S, Ishikawa Y, Matsumoto A, Fujita Y, Nishimura M. Inhibitory effects on microbial growth using the derivatives of benzyl phenyl sulfide. Biocontrol Sci. 2011 Jun;16(2):63-7. doi: 10.4265/bio.16.63. PMID: 21719991. 3. Liang W, Yu Q, Zheng Z, Liu J, Cai Q, Liu S, Lin S. Design and Synthesis of Phenyl Sulfide-Based Cationic Amphiphiles as Membrane-Targeting Antimicrobial Agents against Gram-Positive Pathogens. J Med Chem. 2022 Oct 27;65(20):14221-14236. doi: 10.1021/acs.jmedchem.2c01437. Epub 2022 Oct 18. PMID: 36256884. 4. Kannan GM, Kumar P, Bhaskar AS, Pathak U, Kumar D, Nagar DP, Pant SC, Ganesan K. Prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) against sulfur mustard induced lung toxicity in mice. Drug Chem Toxicol. 2016;39(2):182-9. doi: 10.3109/01480545.2015.1070169. Epub 2015 Aug 6. PMID: 26247826.
In vitro protocol:
1. Lu K, Chen Q, Xu XF, Meng Y, Lin J, Chen WM. Novel benzyl phenyl sulfide derivatives as antibacterial agents against methicillin-resistant Staphylococcus aureus. J Antibiot (Tokyo). 2020 Feb;73(2):82-90. doi: 10.1038/s41429-019-0257-x. Epub 2019 Nov 14. PMID: 31723217. 2. Hatano A, Okada M, Shimazaki K, Uehara S, Ishikawa Y, Matsumoto A, Fujita Y, Nishimura M. Inhibitory effects on microbial growth using the derivatives of benzyl phenyl sulfide. Biocontrol Sci. 2011 Jun;16(2):63-7. doi: 10.4265/bio.16.63. PMID: 21719991.
In vivo protocol:
1. Liang W, Yu Q, Zheng Z, Liu J, Cai Q, Liu S, Lin S. Design and Synthesis of Phenyl Sulfide-Based Cationic Amphiphiles as Membrane-Targeting Antimicrobial Agents against Gram-Positive Pathogens. J Med Chem. 2022 Oct 27;65(20):14221-14236. doi: 10.1021/acs.jmedchem.2c01437. Epub 2022 Oct 18. PMID: 36256884. 2. Kannan GM, Kumar P, Bhaskar AS, Pathak U, Kumar D, Nagar DP, Pant SC, Ganesan K. Prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) against sulfur mustard induced lung toxicity in mice. Drug Chem Toxicol. 2016;39(2):182-9. doi: 10.3109/01480545.2015.1070169. Epub 2015 Aug 6. PMID: 26247826.
1: Kiani A, Dastafkan K. Zinc oxide nanocubes as a destructive nanoadsorbent for the neutralization chemistry of 2-chloroethyl phenyl sulfide: A sulfur mustard simulant. J Colloid Interface Sci. 2016 Sep 15;478:271-9. doi: 10.1016/j.jcis.2016.06.025. Epub 2016 Jun 8. PubMed PMID: 27309947. 2: Kannan GM, Kumar P, Bhaskar AS, Pathak U, Kumar D, Nagar DP, Pant SC, Ganesan K. Prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) against sulfur mustard induced lung toxicity in mice. Drug Chem Toxicol. 2016;39(2):182-9. doi: 10.3109/01480545.2015.1070169. Epub 2015 Aug 6. PubMed PMID: 26247826. 3: Liu SR, Vedamalai M, Wu SP. Hypochlorous acid turn-on boron dipyrromethene probe based on oxidation of methyl phenyl sulfide. Anal Chim Acta. 2013 Oct 24;800:71-6. doi: 10.1016/j.aca.2013.09.018. Epub 2013 Sep 12. PubMed PMID: 24120170. 4: Ludwig G, Kaluđerović GN, Rüffer T, Bette M, Korb M, Block M, Paschke R, Lang H, Steinborn D. Cationic arene ruthenium(II) complexes with chelating P-functionalized alkyl phenyl sulfide and sulfoxide ligands as potent anticancer agents. Dalton Trans. 2013 Mar 21;42(11):3771-4. doi: 10.1039/c3dt33064h. Epub 2013 Jan 23. PubMed PMID: 23340605. 5: Hatano A, Okada M, Shimazaki K, Uehara S, Ishikawa Y, Matsumoto A, Fujita Y, Nishimura M. Inhibitory effects on microbial growth using the derivatives of benzyl phenyl sulfide. Biocontrol Sci. 2011 Jun;16(2):63-7. PubMed PMID: 21719991. 6: Anand T, Vijayaraghavan R, Rao PV, Bansal I, Bhattacharya BK. Attenuation of sulfur mustard toxicity by S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) in mouse liver. Toxicol Mech Methods. 2011 Oct;21(8):596-605. doi: 10.3109/15376516.2011.576713. Epub 2011 May 9. PubMed PMID: 21554084. 7: Maurya MR, Arya A, Kumar A, Pessoa JC. Polystyrene bound oxidovanadium(IV) and dioxidovanadium(V) complexes of histamine derived ligand for the oxidation of methyl phenyl sulfide, diphenyl sulfide and benzoin. Dalton Trans. 2009 Mar 28;(12):2185-95. doi: 10.1039/b814297a. Epub 2009 Feb 3. PubMed PMID: 19274297. 8: Vigo L, Salin P, Oilunkaniemi R, Laitinen RS. catena-Poly[[chlorido(methyl phenyl sulfide-κS)mercury(II)]-μ-chlorido]. Acta Crystallogr Sect E Struct Rep Online. 2008 May 14;64(Pt 6):m809. doi: 10.1107/S1600536808013718. PubMed PMID: 21202494; PubMed Central PMCID: PMC2961523. 9: Baciocchi E, Del Giacco T, Gerini MF, Lanzalunga O. Rates of C-S bond cleavage in tert-alkyl phenyl sulfide radical cations. Org Lett. 2006 Feb 16;8(4):641-4. PubMed PMID: 16468731. 10: Parveen S, Khan MO, Austin SE, Croft SL, Yardley V, Rock P, Douglas KT. Antitrypanosomal, antileishmanial, and antimalarial activities of quaternary arylalkylammonium 2-amino-4-chlorophenyl phenyl sulfides, a new class of trypanothione reductase inhibitor, and of N-acyl derivatives of 2-amino-4-chlorophenyl phenyl sulfide. J Med Chem. 2005 Dec 15;48(25):8087-97. PubMed PMID: 16335933. 11: Rocco F, Bosso SO, Viola F, Milla P, Roma G, Grossi G, Ceruti M. Conjugated methyl sulfide and phenyl sulfide derivatives of oxidosqualene as inhibitors of oxidosqualene and squalene-hopene cyclases. Lipids. 2003 Mar;38(3):201-7. PubMed PMID: 12784859. 12: Mitzel TM, Palomo C, Jendza K. The versatility of alpha-chloropropargyl phenyl sulfide affords high stereo- and regioselectivities in indium-promoted coupling reactions under mild conditions. J Org Chem. 2002 Jan 11;67(1):136-45. PubMed PMID: 11777451. 13: Pasta P, Carrea G, Monzani E, Gaggero N, Colonna S. Chloroperoxidase-catalyzed enantioselective oxidation of methyl phenyl sulfide with dihydroxyfumaric acid/oxygen or ascorbic acid/oxygen as oxidants. Biotechnol Bioeng. 1999 Feb;62(4):489-493. PubMed PMID: 10099556. 14: Miller MW, Mylari BL, Howes HL Jr, Figdor SK, Lynch MJ, Lynch JE, Gupta SK, Chappel LR, Koch RC. Anticoccidial derivatives of 6-azauracil. 4. A 1000-fold enhancement of potency by phenyl sulfide and phenyl sulfone side chains. J Med Chem. 1981 Nov;24(11):1337-42. PubMed PMID: 6895527. 15: HARNISH DP, TARBELL DS. Cleavage of the carbon-sulfur bond; the action of acid catalysts, especially aluminum bromide, on benzyl phenyl sulfide. J Am Chem Soc. 1948 Dec;70(12):4123-7. PubMed PMID: 18105951.